CA1099286A - Procede d'obtention d'halogenures d'acides organiques - Google Patents

Procede d'obtention d'halogenures d'acides organiques

Info

Publication number: CA1099286A
Authority: CA; Canada
Prior art keywords: chloride; reaction; acid; silicon; anhydride
Prior art date: 1977-12-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA317,017A

Other languages

English (en)

Inventor

James D. Johnston

Richmond M. Starrett

Robert N. Sanders

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ethyl Corp

Original Assignee

Ethyl Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-12-28

Filing date

1978-11-28

Publication date

1981-04-14

1978-11-28 Application filed by Ethyl Corp filed Critical Ethyl Corp

1981-04-14 Application granted granted Critical

1981-04-14 Publication of CA1099286A publication Critical patent/CA1099286A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 39
230000008569 process Effects 0.000 title claims abstract description 31
-1 organic acid halide Chemical class 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 16
238000006243 chemical reaction Methods 0.000 claims abstract description 79
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims abstract description 37
239000012346 acetyl chloride Substances 0.000 claims abstract description 36
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims abstract description 34
239000005049 silicon tetrachloride Substances 0.000 claims abstract description 34
239000003054 catalyst Substances 0.000 claims abstract description 25
150000007524 organic acids Chemical class 0.000 claims abstract description 20
229910001507 metal halide Inorganic materials 0.000 claims abstract description 12
150000005309 metal halides Chemical class 0.000 claims abstract description 9
239000002841 Lewis acid Substances 0.000 claims abstract description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 75
150000008064 anhydrides Chemical class 0.000 claims description 27
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 15
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 12
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 9
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 9
230000003197 catalytic effect Effects 0.000 claims description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 5
239000012429 reaction media Substances 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
235000005074 zinc chloride Nutrition 0.000 claims description 3
239000011592 zinc chloride Substances 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 claims 2
150000008065 acid anhydrides Chemical class 0.000 claims 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
239000002904 solvent Substances 0.000 abstract description 20
239000010703 silicon Substances 0.000 abstract description 14
229910052710 silicon Inorganic materials 0.000 abstract description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 10
239000000376 reactant Substances 0.000 abstract description 10
239000000377 silicon dioxide Substances 0.000 abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 17
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 7
239000005711 Benzoic acid Substances 0.000 description 7
238000007792 addition Methods 0.000 description 7
235000010233 benzoic acid Nutrition 0.000 description 7
239000006227 byproduct Substances 0.000 description 7
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 7
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
229910008046 SnC14 Inorganic materials 0.000 description 6
238000004821 distillation Methods 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000011968 lewis acid catalyst Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
229910015400 FeC13 Inorganic materials 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 3
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
JXJTWJYTKGINRZ-UHFFFAOYSA-J silicon(4+);tetraacetate Chemical class [Si+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O JXJTWJYTKGINRZ-UHFFFAOYSA-J 0.000 description 3
XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000010813 internal standard method Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
125000000962 organic group Chemical group 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
150000003377 silicon compounds Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 1
239000010723 turbine oil Substances 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA317,017A 1977-12-28 1978-11-28 Procede d'obtention d'halogenures d'acides organiques Expired CA1099286A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/865,219 US4136113A (en)	1977-12-28	1977-12-28	Process for preparation of organic acid halide
US865,219		1977-12-28

Publications (1)

Publication Number	Publication Date
CA1099286A true CA1099286A (fr)	1981-04-14

Family

ID=25344975

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA317,017A Expired CA1099286A (fr)	1977-12-28	1978-11-28	Procede d'obtention d'halogenures d'acides organiques

Country Status (6)

Country	Link
US (1)	US4136113A (fr)
EP (1)	EP0002989B1 (fr)
JP (1)	JPS5495507A (fr)
CA (1)	CA1099286A (fr)
DE (1)	DE2861221D1 (fr)
IT (1)	IT1110878B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5612336A (en) *	1979-07-10	1981-02-06	Seitetsu Kagaku Co Ltd	Preparation of alpha-bromocarboxylic acid halide
DE3129273A1 (de) *	1981-07-24	1983-02-10	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von aldehyden
JPS59190828U (ja) *	1983-06-03	1984-12-18	株式会社アイジー技術研究所	サイデイングボ−ド
US4693851A (en) *	1985-04-09	1987-09-15	Raychem Corporation	Purification of acid halides
DE4313793A1 (de) *	1993-04-27	1994-11-03	Solvay Fluor & Derivate	Herstellung von Carbonsäurehalogeniden und Carboxylat-Salzen
CN105777531A (zh) *	2015-12-28	2016-07-20	四川理工学院	一种用四氯化硅制备肉桂酰氯的方法
CN105601501A (zh) *	2016-02-29	2016-05-25	四川理工学院	一种用四氯化硅制备三氯乙酰氯的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US944372A (en) *	1909-03-18	1909-12-28	Consortium Elektrochem Ind	Process of preparing organic compounds containing the acetyl group.
US1805162A (en) *	1928-10-11	1931-05-12	Dow Chemical Co	Preparation of aliphatic acid chlorides

1977
- 1977-12-28 US US05/865,219 patent/US4136113A/en not_active Expired - Lifetime
1978
- 1978-11-28 CA CA317,017A patent/CA1099286A/fr not_active Expired
- 1978-12-21 DE DE7878400254T patent/DE2861221D1/de not_active Expired
- 1978-12-21 EP EP78400254A patent/EP0002989B1/fr not_active Expired
- 1978-12-27 JP JP16452978A patent/JPS5495507A/ja active Granted
- 1978-12-27 IT IT52454/78A patent/IT1110878B/it active

Also Published As

Publication number	Publication date
IT7852454A0 (it)	1978-12-27
DE2861221D1 (en)	1981-12-24
EP0002989B1 (fr)	1981-10-21
JPS565728B2 (fr)	1981-02-06
IT1110878B (it)	1986-01-06
JPS5495507A (en)	1979-07-28
EP0002989A1 (fr)	1979-07-11
US4136113A (en)	1979-01-23

Legal Events

Date	Code	Title	Description
1998-04-14	MKEX	Expiry

Publication	Publication Date	Title
US5481028A (en)	1996-01-02	Lewis acid catalyzed conjugated iodofluorination of fluoroolefins
US4214105A (en)	1980-07-22	Process for the hydroxylation of phenol
US5527966A (en)	1996-06-18	Preparation of triphenylphosphine
CA1099286A (fr)	1981-04-14	Procede d'obtention d'halogenures d'acides organiques
DE69624959T2 (de)	2003-07-17	Herstellung von Pentafluorphenylverbindungen
US1965556A (en)	1934-07-03	Method for the preparation of acid halides
US4912269A (en)	1990-03-27	Synthesis of perfluoroalkyl bromides
US4167525A (en)	1979-09-11	Process for preparation of aromatic acyl chloride
US5177238A (en)	1993-01-05	Preparation of dialkyl allylphosphonic acid diesters
JPH0228587B2 (ja)	1990-06-25	Shibosankuroraidonoseizohoho
US4169847A (en)	1979-10-02	Process for the manufacture of α-chloroalkanoyl chlorides
EP0460589A1 (fr)	1991-12-11	Procédé de préparation de cyclopentyl trichlorosilane
US4374264A (en)	1983-02-15	Process for the preparation of γ-unsaturated carboxylates
US3590104A (en)	1971-06-29	Process for preparing 0,0-dialkyl-0-phenyl phosphorothioates
US5847236A (en)	1998-12-08	Process for the preparation of 2-chloro-4-methylphenol
JPH08231462A (ja)	1996-09-10	パーフルオロアルキルカルボン酸フルオライド及びその誘導体の製造方法
IE42100B1 (en)	1980-06-04	Process for the preparation of 2,2,2-trichloroethyl chloroformate
JPS61267538A (ja)	1986-11-27	２−アルキル−６−アシルナフタリンの製造法
EP0038223B1 (fr)	1984-08-08	Procédé pour la préparation d'halogénures d'acides trifluorométhylbenzoiques
US4122115A (en)	1978-10-24	Preparation of chloro- and bromo-fluoroacetyl chloride
US3303226A (en)	1967-02-07	Isomer trans, trans, trans-cyclododecatriene-(1, 5, 9) preparation
US4130594A (en)	1978-12-19	Liquid phase fluorination process
JPH0137388B2 (fr)	1989-08-07
JPH04164063A (ja)	1992-06-09	クロロスルホニルイソシアナートの製造方法
US4503025A (en)	1985-03-05	Process for preparing dicyanogen